# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_teste1

_audit_creation_date             2011-12-01T18:03:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_name_common            'Pyridoxal phenylene molybdenum complex'
_chemical_formula_moiety         'C18 H28 Mo N3 O8.50 S2'
_chemical_formula_sum            'C18 H28 Mo N3 O8.50 S2'
_chemical_formula_weight         582.49
_chemical_melting_point          473K


#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6409(2)
_cell_length_b                   9.7269(2)
_cell_length_c                   13.3073(2)
_cell_angle_alpha                74.4380(10)
_cell_angle_beta                 81.1780(10)
_cell_angle_gamma                80.1810(10)
_cell_volume                     1176.91(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4557
_cell_measurement_theta_min      2.194
_cell_measurement_theta_max      25.0745


#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.046
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             598
_exptl_special_details           
;
?
;


#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9276
_exptl_absorpt_correction_T_max  0.9836


#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_number            19189
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         26.79
_diffrn_reflns_theta_full        26.79
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             4998
_reflns_number_gt                3465
_reflns_threshold_expression     >2sigma(I)


#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'


#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0719P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4998
_refine_ls_number_parameters     274
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.533
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.267
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.112


#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo Mo 0.96277(7) 0.50137(6) 0.86474(4) 0.0310(2) Uani 1 1 d . . .
S2 S 0.4635(2) 0.3679(3) 0.80260(19) 0.0584(6) Uani 1 1 d . . .
S1 S 0.4206(3) 0.0035(3) 0.6954(2) 0.0649(7) Uani 1 1 d . . .
O4 O 0.8028 0.3392 0.9444 0.038 Uani 1 1 d D . .
O6 O 0.928 0.0156 0.6192 0.043 Uani 1 1 d . . .
H6 H 1.0057 -0.0296 0.6064 0.065 Uiso 1 1 calc R . .
O1 O 1.0841(6) 0.6033(5) 0.7870(4) 0.0416(13) Uani 1 1 d . . .
N3 N 0.8956 0.2899 0.628 0.0296(13) Uani 1 1 d D . .
O2 O 0.8086(6) 0.6161(5) 0.8500(4) 0.0403(13) Uani 1 1 d . . .
O5 O 1.0964(5) 0.3111(5) 0.8776(3) 0.0321(11) Uani 1 1 d . . .
N1 N 1.1518(6) -0.0711(6) 0.9219(4) 0.0319(13) Uani 1 1 d . . .
O9 O 0.1609 -0.1817 0.6073 0.0538(15) Uani 1 1 d . . .
N2 N 0.9214(6) 0.4277(6) 0.7313(4) 0.0252(12) Uani 1 1 d . . .
C3 C 1.0023(7) 0.1657(7) 0.7920(5) 0.0270(14) Uani 1 1 d . . .
C1 C 1.1640(7) 0.0615(7) 0.9256(5) 0.0281(15) Uani 1 1 d . . .
O8 O 0.6069(7) 0.2913(8) 0.8262(5) 0.075(2) Uani 1 1 d . . .
O3 O 1 0.5 1 0.0440(19) Uani 1 2 d S . .
C13 C 0.8344(7) 0.6659(7) 0.6096(5) 0.0329(16) Uani 1 1 d . . .
H13 H 0.8463 0.7253 0.6511 0.039 Uiso 1 1 calc R . .
C9 C 0.8515(7) 0.4301(7) 0.5766(5) 0.0298(15) Uani 1 1 d . . .
C7 C 0.8895(8) -0.0151(8) 0.7296(5) 0.0368(17) Uani 1 1 d . . .
H7A H 0.8829 -0.1173 0.7554 0.044 Uiso 1 1 calc R . .
H7B H 0.7961 0.0365 0.7434 0.044 Uiso 1 1 calc R . .
C12 C 0.7839(8) 0.7218(8) 0.5128(6) 0.0425(19) Uani 1 1 d . . .
H12 H 0.7597 0.8209 0.4898 0.051 Uiso 1 1 calc R . .
C8 C 0.9389(7) 0.2934(7) 0.7203(5) 0.0249(14) Uani 1 1 d . . .
C5 C 1.0644(7) -0.0883(7) 0.8572(5) 0.0333(16) Uani 1 1 d . . .
H5 H 1.0537 -0.1817 0.8575 0.04 Uiso 1 1 calc R . .
C4 C 0.9904(7) 0.0240(7) 0.7911(5) 0.0287(15) Uani 1 1 d . . .
O7 O 0.4034(8) -0.1096(10) 0.6425(6) 0.096(3) Uani 1 1 d . . .
C11 C 0.7683(8) 0.6353(9) 0.4491(5) 0.0427(19) Uani 1 1 d . . .
H11 H 0.7351 0.6779 0.3843 0.051 Uiso 1 1 calc R . .
C10 C 0.8006(8) 0.4885(8) 0.4791(5) 0.0382(18) Uani 1 1 d . . .
H10 H 0.7892 0.4304 0.4365 0.046 Uiso 1 1 calc R . .
C14 C 0.8664(7) 0.5177(7) 0.6417(5) 0.0291(15) Uani 1 1 d . . .
C6 C 1.2634(8) 0.0793(8) 0.9967(5) 0.0392(18) Uani 1 1 d . . .
H6A H 1.307 -0.0138 1.0322 0.059 Uiso 1 1 calc R . .
H6B H 1.2113 0.1282 1.0475 0.059 Uiso 1 1 calc R . .
H6C H 1.3352 0.1348 0.9557 0.059 Uiso 1 1 calc R . .
C2 C 1.0860(7) 0.1849(7) 0.8646(5) 0.0275(15) Uani 1 1 d . . .
C16 C 0.5583(10) 0.0944(13) 0.6163(8) 0.076(3) Uani 1 1 d . . .
H16A H 0.5245 0.153 0.5521 0.114 Uiso 1 1 calc R . .
H16B H 0.6367 0.0252 0.6007 0.114 Uiso 1 1 calc R . .
H16C H 0.5885 0.1543 0.6533 0.114 Uiso 1 1 calc R . .
C18 C 0.3959(12) 0.4558(15) 0.9030(9) 0.094(4) Uani 1 1 d . . .
H18A H 0.3746 0.3856 0.9673 0.141 Uiso 1 1 calc R . .
H18B H 0.3112 0.5196 0.8842 0.141 Uiso 1 1 calc R . .
H18C H 0.4652 0.5102 0.9122 0.141 Uiso 1 1 calc R . .
C17 C 0.4902(12) 0.5204(13) 0.6986(9) 0.097(4) Uani 1 1 d . . .
H17A H 0.5285 0.4904 0.6357 0.146 Uiso 1 1 calc R . .
H17B H 0.5552 0.573 0.7157 0.146 Uiso 1 1 calc R . .
H17C H 0.4014 0.5811 0.6877 0.146 Uiso 1 1 calc R . .
C15 C 0.5119(11) -0.0908(13) 0.8049(8) 0.078(3) Uani 1 1 d . . .
H15A H 0.4497 -0.1474 0.8567 0.117 Uiso 1 1 calc R . .
H15B H 0.543 -0.0231 0.8345 0.117 Uiso 1 1 calc R . .
H15C H 0.5925 -0.1529 0.7827 0.117 Uiso 1 1 calc R . .
H4A H 0.7384 0.3257 0.9047 0.053 Uiso 1 1 d D . .
H4B H 0.8145 0.2365 0.9828 0.043 Uiso 1 1 d D . .
H8B H 0.256 -0.2178 0.6033 0.333 Uiso 1 1 d . . .
H3 H 0.9011 0.2113 0.5937 0.08(3) Uiso 1 1 d D . .
H8A H 0.1007 -0.2555 0.6647 0.21(7) Uiso 1 1 d . . .




#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo O1 1.702(5) . ?
Mo O2 1.703(5) . ?
Mo O3 1.8848(5) . ?
Mo O5 2.049(4) . ?
Mo N2 2.197(5) . ?
Mo O4 2.3279(6) . ?
S2 O8 1.491(6) . ?
S2 C18 1.760(10) . ?
S2 C17 1.761(12) . ?
S1 O7 1.499(8) . ?
S1 C16 1.768(11) . ?
S1 C15 1.772(9) . ?
O6 C7 1.422(7) . ?
N3 C8 1.367(5) . ?
N3 C9 1.378(7) . ?
O5 C2 1.307(7) . ?
N1 C1 1.329(8) . ?
N1 C5 1.352(8) . ?
N2 C8 1.333(8) . ?
N2 C14 1.394(8) . ?
C3 C4 1.406(9) . ?
C3 C2 1.416(8) . ?
C3 C8 1.452(9) . ?
C1 C2 1.422(9) . ?
C1 C6 1.505(9) . ?
O3 Mo 1.8848(5) 2_767 ?
C13 C12 1.386(9) . ?
C13 C14 1.383(9) . ?
C9 C10 1.397(9) . ?
C9 C14 1.405(8) . ?
C7 C4 1.516(9) . ?
C12 C11 1.383(10) . ?
C5 C4 1.374(9) . ?
C11 C10 1.369(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mo O2 102.4(3) . . ?
O1 Mo O3 101.68(15) . . ?
O2 Mo O3 102.79(15) . . ?
O1 Mo O5 94.5(2) . . ?
O2 Mo O5 157.7(2) . . ?
O3 Mo O5 87.79(11) . . ?
O1 Mo N2 91.2(2) . . ?
O2 Mo N2 87.4(2) . . ?
O3 Mo N2 161.28(14) . . ?
O5 Mo N2 77.62(17) . . ?
O1 Mo O4 168.70(15) . . ?
O2 Mo O4 80.76(18) . . ?
O3 Mo O4 88.05(2) . . ?
O5 Mo O4 80.05(14) . . ?
N2 Mo O4 78.02(14) . . ?
O8 S2 C18 107.2(5) . . ?
O8 S2 C17 106.5(5) . . ?
C18 S2 C17 98.7(6) . . ?
O7 S1 C16 105.3(5) . . ?
O7 S1 C15 105.1(5) . . ?
C16 S1 C15 99.0(5) . . ?
C8 N3 C9 107.2(4) . . ?
C2 O5 Mo 134.2(4) . . ?
C1 N1 C5 118.9(6) . . ?
C8 N2 C14 107.3(5) . . ?
C8 N2 Mo 128.2(4) . . ?
C14 N2 Mo 124.5(4) . . ?
C4 C3 C2 117.9(6) . . ?
C4 C3 C8 124.1(5) . . ?
C2 C3 C8 118.0(6) . . ?
N1 C1 C2 121.7(6) . . ?
N1 C1 C6 118.4(6) . . ?
C2 C1 C6 120.0(6) . . ?
Mo O3 Mo 180 2_767 . ?
C12 C13 C14 116.9(6) . . ?
N3 C9 C10 131.4(5) . . ?
N3 C9 C14 107.1(5) . . ?
C10 C9 C14 121.5(6) . . ?
O6 C7 C4 115.0(6) . . ?
C13 C12 C11 122.3(7) . . ?
N2 C8 N3 111.0(5) . . ?
N2 C8 C3 126.1(5) . . ?
N3 C8 C3 122.8(5) . . ?
N1 C5 C4 123.8(6) . . ?
C5 C4 C3 118.7(6) . . ?
C5 C4 C7 116.6(6) . . ?
C3 C4 C7 124.3(6) . . ?
C10 C11 C12 121.6(6) . . ?
C11 C10 C9 116.9(6) . . ?
C13 C14 N2 131.9(6) . . ?
C13 C14 C9 120.7(6) . . ?
N2 C14 C9 107.4(5) . . ?
O5 C2 C3 123.1(6) . . ?
O5 C2 C1 118.1(5) . . ?
C3 C2 C1 118.7(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Mo O5 C2 -129.8(8) . . . . ?
O2 Mo O5 C2 9.4(12) . . . . ?
O3 Mo O5 C2 128.6(8) . . . . ?
N2 Mo O5 C2 -39.5(8) . . . . ?
O4 Mo O5 C2 40.2(8) . . . . ?
O1 Mo N2 C8 119.5(8) . . . . ?
O2 Mo N2 C8 -138.1(8) . . . . ?
O3 Mo N2 C8 -14.5(12) . . . . ?
O5 Mo N2 C8 25.1(7) . . . . ?
O4 Mo N2 C8 -57.1(7) . . . . ?
O1 Mo N2 C14 -62.6(7) . . . . ?
O2 Mo N2 C14 39.8(7) . . . . ?
O3 Mo N2 C14 163.4(5) . . . . ?
O5 Mo N2 C14 -157.0(7) . . . . ?
O4 Mo N2 C14 120.8(7) . . . . ?
C5 N1 C1 C2 1.1(13) . . . . ?
C5 N1 C1 C6 -179.0(9) . . . . ?
O1 Mo O3 Mo -12E1(10) . . . 2_767 ?
O2 Mo O3 Mo 14E1(10) . . . 2_767 ?
O5 Mo O3 Mo -3E1(10) . . . 2_767 ?
N2 Mo O3 Mo 1E1(10) . . . 2_767 ?
O4 Mo O3 Mo 6E1(10) . . . 2_767 ?
C8 N3 C9 C10 178.1(10) . . . . ?
C8 N3 C9 C14 -1.3(10) . . . . ?
C14 C13 C12 C11 -1.6(16) . . . . ?
C14 N2 C8 N3 -0.8(10) . . . . ?
Mo N2 C8 N3 177.4(6) . . . . ?
C14 N2 C8 C3 176.1(9) . . . . ?
Mo N2 C8 C3 -5.7(13) . . . . ?
C9 N3 C8 N2 1.3(10) . . . . ?
C9 N3 C8 C3 -175.7(8) . . . . ?
C4 C3 C8 N2 165.1(9) . . . . ?
C2 C3 C8 N2 -17.9(14) . . . . ?
C4 C3 C8 N3 -18.4(14) . . . . ?
C2 C3 C8 N3 158.6(8) . . . . ?
C1 N1 C5 C4 2.3(14) . . . . ?
N1 C5 C4 C3 -1.6(15) . . . . ?
N1 C5 C4 C7 -175.6(9) . . . . ?
C2 C3 C4 C5 -2.4(13) . . . . ?
C8 C3 C4 C5 174.5(9) . . . . ?
C2 C3 C4 C7 171.1(9) . . . . ?
C8 C3 C4 C7 -11.9(14) . . . . ?
O6 C7 C4 C5 -112.7(9) . . . . ?
O6 C7 C4 C3 73.6(11) . . . . ?
C13 C12 C11 C10 0.6(17) . . . . ?
C12 C11 C10 C9 -0.3(16) . . . . ?
N3 C9 C10 C11 -178.4(10) . . . . ?
C14 C9 C10 C11 1.0(15) . . . . ?
C12 C13 C14 N2 177.9(10) . . . . ?
C12 C13 C14 C9 2.3(14) . . . . ?
C8 N2 C14 C13 -176.1(10) . . . . ?
Mo N2 C14 C13 5.7(14) . . . . ?
C8 N2 C14 C9 0.0(10) . . . . ?
Mo N2 C14 C9 -178.3(6) . . . . ?
N3 C9 C14 C13 177.4(9) . . . . ?
C10 C9 C14 C13 -2.1(15) . . . . ?
N3 C9 C14 N2 0.8(10) . . . . ?
C10 C9 C14 N2 -178.7(9) . . . . ?
Mo O5 C2 C1 -149.9(7) . . . . ?
Mo O5 C2 C3 30.8(13) . . . . ?
N1 C1 C2 O5 175.6(8) . . . . ?
C6 C1 C2 O5 -4.2(13) . . . . ?
N1 C1 C2 C3 -5.1(13) . . . . ?
C6 C1 C2 C3 175.1(8) . . . . ?
C4 C3 C2 O5 -175.1(8) . . . . ?
C8 C3 C2 O5 7.7(13) . . . . ?
C4 C3 C2 C1 5.6(13) . . . . ?
C8 C3 C2 C1 -171.5(8) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 861363'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_added_by_encifer
#\#CIF_1.1

#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2013-03-21 at 16:22:49
#  Using CIFtbx version 2.6.2 16 Jun 1998

#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.3
#  Request file    : \wingx\files\archive.dat
#  CIF files read  : teste sec222



_audit_creation_date             2013-03-21T16:22:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
4-(1H-benzo imidazol-2-yl)-5-(hydroxymethyl)-2-methylpyridin-3-ol chloride salt
;
_chemical_name_common            'pyridoxal imidazol salt'
_chemical_formula_moiety         'C14 H14 Cl N3 O2'
_chemical_formula_sum            'C14 H14 Cl N3 O2'
_chemical_formula_weight         291.73
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8031(13)
_cell_length_b                   4.9069(6)
_cell_length_c                   24.726(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.434(8)
_cell_angle_gamma                90
_cell_volume                     1289.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1450
_cell_measurement_theta_min      2.8715
_cell_measurement_theta_max      21.442

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9449
_exptl_absorpt_correction_T_max  0.9734

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_number            21513
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_full        28.43
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             3240
_reflns_number_gt                1548
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0477P)²+0.1791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3240
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.094
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl -0.10426(6) -0.01528(16) 0.06739(3) 0.0548(3) Uani 1 1 d . . .
O1 O 0.36723(16) 0.9209(4) -0.00682(7) 0.0442(5) Uani 1 1 d . . .
O2 O 0.20618(17) 0.8902(4) 0.19329(7) 0.0490(5) Uani 1 1 d . . .
N2 N 0.48056(19) 1.1057(5) 0.10227(10) 0.0372(6) Uani 1 1 d . . .
N1 N 0.10507(19) 0.4229(5) 0.08626(9) 0.0390(6) Uani 1 1 d . . .
N3 N 0.38724(18) 1.1539(4) 0.17406(8) 0.0381(5) Uani 1 1 d . . .
C7 C 0.3677(2) 0.6691(6) 0.02145(10) 0.0426(7) Uani 1 1 d . . .
H7A H 0.4523 0.6349 0.0412 0.051 Uiso 1 1 calc R . .
H7B H 0.3468 0.5249 -0.0055 0.051 Uiso 1 1 calc R . .
C4 C 0.2785(2) 0.6530(5) 0.06149(10) 0.0348(6) Uani 1 1 d . . .
C3 C 0.2908(2) 0.8112(5) 0.11008(9) 0.0324(6) Uani 1 1 d . . .
C8 C 0.3854(2) 1.0203(5) 0.12728(10) 0.0333(6) Uani 1 1 d . . .
C10 C 0.5477(2) 1.3041(5) 0.13482(10) 0.0348(6) Uani 1 1 d . . .
C11 C 0.6514(2) 1.4613(6) 0.12928(11) 0.0451(7) Uani 1 1 d . . .
H11 H 0.693 1.4397 0.0998 0.054 Uiso 1 1 calc R . .
C12 C 0.6893(2) 1.6513(6) 0.16988(11) 0.0462(7) Uani 1 1 d . . .
H12 H 0.7572 1.7639 0.1671 0.055 Uiso 1 1 calc R . .
C5 C 0.1838(2) 0.4653(5) 0.05068(11) 0.0392(6) Uani 1 1 d . . .
H5 H 0.1736 0.3653 0.0182 0.047 Uiso 1 1 calc R . .
C1 C 0.1123(2) 0.5587(5) 0.13318(10) 0.0372(6) Uani 1 1 d . . .
C2 C 0.2052(2) 0.7598(5) 0.14584(10) 0.0356(6) Uani 1 1 d . . .
C9 C 0.4873(2) 1.3314(5) 0.17966(10) 0.0349(6) Uani 1 1 d . . .
C14 C 0.5282(2) 1.5204(5) 0.22064(11) 0.0428(7) Uani 1 1 d . . .
H14 H 0.4887 1.5381 0.2509 0.051 Uiso 1 1 calc R . .
C13 C 0.6294(2) 1.6806(6) 0.21497(11) 0.0465(7) Uani 1 1 d . . .
H13 H 0.6583 1.8106 0.2416 0.056 Uiso 1 1 calc R . .
C6 C 0.0239(2) 0.4945(6) 0.17043(12) 0.0516(8) Uani 1 1 d . . .
H6A H -0.0322 0.3524 0.1546 0.077 Uiso 1 1 calc R . .
H6B H -0.0238 0.6544 0.1756 0.077 Uiso 1 1 calc R . .
H6C H 0.0703 0.4351 0.2053 0.077 Uiso 1 1 calc R . .
H011 H 0.041(3) 0.290(7) 0.0773(12) 0.085(11) Uiso 1 1 d . . .
H01 H 0.279(3) 0.953(8) -0.0249(14) 0.110(13) Uiso 1 1 d . . .
H02 H 0.490(2) 1.060(5) 0.0735(10) 0.035(8) Uiso 1 1 d . . .
H022 H 0.278(3) 1.017(7) 0.1963(13) 0.089(11) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.419(3) . ?
O1 H01 0.99(3) . ?
O2 C2 1.335(3) . ?
O2 H022 0.98(3) . ?
N2 C8 1.358(3) . ?
N2 C10 1.382(3) . ?
N2 H02 0.77(2) . ?
N1 C1 1.328(3) . ?
N1 C5 1.346(3) . ?
N1 H011 0.95(3) . ?
N3 C8 1.327(3) . ?
N3 C9 1.375(3) . ?
C7 C4 1.504(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C4 C5 1.366(3) . ?
C4 C3 1.416(3) . ?
C3 C2 1.413(3) . ?
C3 C8 1.456(3) . ?
C10 C11 1.387(3) . ?
C10 C9 1.391(3) . ?
C11 C12 1.377(4) . ?
C11 H11 0.93 . ?
C12 C13 1.394(4) . ?
C12 H12 0.93 . ?
C5 H5 0.93 . ?
C1 C2 1.402(3) . ?
C1 C6 1.476(4) . ?
C9 C14 1.386(3) . ?
C14 C13 1.374(3) . ?
C14 H14 0.93 . ?
C13 H13 0.93 . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H01 106(2) . . ?
C2 O2 H022 104.4(19) . . ?
C8 N2 C10 108.2(2) . . ?
C8 N2 H02 124.9(19) . . ?
C10 N2 H02 126.6(19) . . ?
C1 N1 C5 123.3(2) . . ?
C1 N1 H011 118.4(19) . . ?
C5 N1 H011 118.3(19) . . ?
C8 N3 C9 106.7(2) . . ?
O1 C7 C4 115.1(2) . . ?
O1 C7 H7A 108.5 . . ?
C4 C7 H7A 108.5 . . ?
O1 C7 H7B 108.5 . . ?
C4 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 C7 116.9(2) . . ?
C3 C4 C7 123.8(2) . . ?
C2 C3 C4 117.5(2) . . ?
C2 C3 C8 116.6(2) . . ?
C4 C3 C8 126.0(2) . . ?
N3 C8 N2 110.6(2) . . ?
N3 C8 C3 120.1(2) . . ?
N2 C8 C3 129.3(2) . . ?
N2 C10 C11 133.0(2) . . ?
N2 C10 C9 105.0(2) . . ?
C11 C10 C9 121.9(2) . . ?
C12 C11 C10 116.3(2) . . ?
C12 C11 H11 121.8 . . ?
C10 C11 H11 121.8 . . ?
C11 C12 C13 122.2(3) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
N1 C5 C4 121.0(2) . . ?
N1 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
N1 C1 C2 118.4(2) . . ?
N1 C1 C6 119.7(2) . . ?
C2 C1 C6 121.9(2) . . ?
O2 C2 C1 115.2(2) . . ?
O2 C2 C3 124.2(2) . . ?
C1 C2 C3 120.6(2) . . ?
N3 C9 C14 129.7(2) . . ?
N3 C9 C10 109.4(2) . . ?
C14 C9 C10 120.9(2) . . ?
C13 C14 C9 117.6(2) . . ?
C13 C14 H14 121.2 . . ?
C9 C14 H14 121.2 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C4 C5 116.7(3) . . . . ?
O1 C7 C4 C3 -66.1(3) . . . . ?
C5 C4 C3 C2 1.7(3) . . . . ?
C7 C4 C3 C2 -175.5(2) . . . . ?
C5 C4 C3 C8 -179.4(2) . . . . ?
C7 C4 C3 C8 3.5(4) . . . . ?
C9 N3 C8 N2 -0.2(3) . . . . ?
C9 N3 C8 C3 178.7(2) . . . . ?
C10 N2 C8 N3 0.3(3) . . . . ?
C10 N2 C8 C3 -178.5(2) . . . . ?
C2 C3 C8 N3 -0.8(3) . . . . ?
C4 C3 C8 N3 -179.7(2) . . . . ?
C2 C3 C8 N2 177.9(2) . . . . ?
C4 C3 C8 N2 -1.0(4) . . . . ?
C8 N2 C10 C11 -179.1(3) . . . . ?
C8 N2 C10 C9 -0.3(3) . . . . ?
N2 C10 C11 C12 177.0(3) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C10 C11 C12 C13 1.6(4) . . . . ?
C1 N1 C5 C4 0.7(4) . . . . ?
C3 C4 C5 N1 -2.1(4) . . . . ?
C7 C4 C5 N1 175.2(2) . . . . ?
C5 N1 C1 C2 1.2(4) . . . . ?
C5 N1 C1 C6 -178.6(2) . . . . ?
N1 C1 C2 O2 179.3(2) . . . . ?
C6 C1 C2 O2 -1.0(4) . . . . ?
N1 C1 C2 C3 -1.6(4) . . . . ?
C6 C1 C2 C3 178.2(2) . . . . ?
C4 C3 C2 O2 179.2(2) . . . . ?
C8 C3 C2 O2 0.2(3) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
C8 C3 C2 C1 -178.9(2) . . . . ?
C8 N3 C9 C14 178.5(3) . . . . ?
C8 N3 C9 C10 0.0(3) . . . . ?
N2 C10 C9 N3 0.2(3) . . . . ?
C11 C10 C9 N3 179.2(2) . . . . ?
N2 C10 C9 C14 -178.5(2) . . . . ?
C11 C10 C9 C14 0.6(4) . . . . ?
N3 C9 C14 C13 -177.6(2) . . . . ?
C10 C9 C14 C13 0.7(4) . . . . ?
C9 C14 C13 C12 -0.7(4) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 861364'
